Water → Dimethyl 2-fluoro-5-methylbenzene-1,4-dicarboxylate

HRID 389105Notes

Reaction equation

HRID 389105 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].IC.[F:9][C:10]1[CH:18]=[C:17]([C:19](O)=[O:20])[C:16]([CH3:22])=[CH:15][C:11]=1[C:12]([OH:14])=[O:13].O.CN([CH:27]=[O:28])C>>[F:9][C:10]1[CH:18]=[C:17]([C:19]([O:28][CH3:27])=[O:20])[C:16]([CH3:22])=[CH:15][C:11]=1[C:12]([O:14][CH3:1])=[O:13]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 58243772HCID 58243772, compound

Product 1

HCID 56965483Dimethyl 2-fluoro-5-methylbenzene-1,4-dicarboxylate

Procedure

Potassium carbonate (1.2 g) and iodomethane (0.7 ml) were added to a solution of 2-fluoro-5-methylterephthalic acid (755 mg) in DMF (5 ml), followed by stirring at room temperature overnight. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was further washed with water and then saturated brine, the solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 90:10), and the solvent was evaporated under reduced pressure to obtain, as a colorless solid, dimethyl 2-fluoro-5-methylterephthalate (708 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was further washed with water
  3. customsaturated brine, the solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 90:10)
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ce1b9ca879cd487db3d9156d8737486e
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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